Sodium Hydroxide → 3-Chloro-4-ethoxybenzoic acid

HRID 2189738Notes

Reaction equation

HRID 2189738 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[C:5]([O:7]C)=[O:6].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20110212Methyl 3-chloro-4-ethoxybenzoate

Product 1

HCID 7209893-Chloro-4-ethoxybenzoic acidYield 78.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of Methyl 3-chloro-4-(ethyloxy)benzoate (D6) (11.24 g, 52.4 mmol) in methanol (40 ml) was added 2M aq. NaOH (40 ml) and the resultant mixture was heated at 60° C. for 2 hours. The reaction mixture was partitioned between EtOAc and dilute hydrochloric acid. The organics were separated, dried and evaporated in vacuo to give the crude product. This material was triturated with ether to give the title compound as a white solid (8.21 g). MS (ES): C9H935ClO3 requires 200; found (MH+) 201.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and dilute hydrochloric acid
  2. customThe organics were separated
  3. customdried
  4. customevaporated in vacuo
  5. customto give the crude product
  6. customThis material was triturated with ether

Sources & evidence

ORD record
ord-686e5b1d38c24831b8682f4fc7094fd8
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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